CN103772362A - Pyrene-imidazole derivative and application thereof as electroluminescent material - Google Patents

Pyrene-imidazole derivative and application thereof as electroluminescent material Download PDF

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CN103772362A
CN103772362A CN201410004106.9A CN201410004106A CN103772362A CN 103772362 A CN103772362 A CN 103772362A CN 201410004106 A CN201410004106 A CN 201410004106A CN 103772362 A CN103772362 A CN 103772362A
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pyrene
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路萍
刘豫龙
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Jilin University
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    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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    • C07—ORGANIC CHEMISTRY
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
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    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms

Abstract

The invention relates to a pyrene-imidazole derivative and application thereof as an electroluminescent material, belonging to the technical field of organic electroluminescence. The pyrene-imidazole derivative is a blue fluorescence radiation material with the bipolar carrier transport property, and comprises triphenylamine with the hole transport property, a carbazole unit, and an imidazole unit with the electrical transmission property. The synthesis method of the compound is simple and can be widely used. The material has the bipolar carrier transport property, can be used alone as a luminous layer and a carrier transport layer, also can be doped with other dye to be used as the luminous layer and the carrier transport layer. The compound has strong luminescent property in solution and solid states, can form a uniform membrane, and has good optical and thermal stability.

Description

Pyrene benzimidazole derivative and as the application of electroluminescent material
Technical field
The invention belongs to technical field of organic electroluminescence, be specifically related to a class and have blue-fluorescence luminescent material---pyrene benzimidazole derivative and the application in electroluminescent field as electroluminescent material thereof of one pole or bipolar carrier transmission performance.
Background technology
From Tang in 1987 and Van Slyke (Appl.Phys.Lett.1987,51 (12) .21) report Organic Light Emitting Diode (organic light emitting diodes, OLEDs) since, significant progress, through the development of two more than ten years, is all being obtained in electroluminescent field aspect material system, device application and correlation theory.Electroluminescent device of organic thin film have from main light emission, low-voltage direct-current drive, entirely solidify, a series of advantage such as visual angle is wide, color is abundant, gather around and have broad application prospects.
The typical structure of OLED comprises cathode layer, anode layer, and organic luminous layer between this is two-layer, can comprise one or more functional layers in electron transfer layer, hole transmission layer and luminescent layer in organic luminous layer.Ambipolar carrier transmission material has electronics and hole transport performance concurrently, can balancing device in injection and the transmission of current carrier, simplify device architecture, cost-saving, thereby be subject to extensive concern.In recent years, glyoxaline compound, particularly aromatics imdazole derivatives, due to its unique electronic structure, obtained research widely in electroluminescent field.If the patent No. is 5,646, in 948 United States Patent (USP), relate to a kind of compound of imidazoles, this compound couples together three benzoglyoxaline groups by phenyl group, whole material has showed good film-forming properties and high thermodynamic stability, particularly excellent electronic injection performance, becomes now most widely used electronic injection layer material and luminous material of main part.
Pyrene is a typical condensed-nuclei aromatics, the tendency that pyrene and derivative thereof generally have higher quantum yield, longer fluorescence lifetime, excellent light stability and the susceptibility that microenvironment is changed and be easy to form excimer.Pyrene is the two dimensional structure of aromaticity, has stronger π-electron delocalized energy, and pyrene and derivative thereof have been studied widely and reported as electroluminescent material.As (the Li X G of Li report, Liu Y W, Huang M R, et al.Simple efficient synthesis of strongly luminescent polypyrene with intrinsic conductivity and high carbon yield by chemical oxidative polymerization of pyrene[J] .Chem.Eur.J.2010, 16, 4803 ?4813) by chemical oxidization method, pyrene monomer polymerization is become to the poly-pyrene that fluorescent emission ability is stronger, especially replace by chain alkyl the polymkeric substance that pyrene derivatives forms, after polymerization, obtain the fluorescent polymer of solubility, give material good film forming processibility, make it be easy to device, easy to use.The derivative (Chem.Rev.2011,111,7260 – 7314) of the pyrene of the research group such as Klaus M ü llen report, not only can emitting fluorescence, and can be used as hole or electron transport material.Because π ?pi accumulation between stiff molecule can cause the remarkable cancellation of solid state fluorescence that forms excimers (excimer) and cause material, so it is significant to show the pyrene class luminescent material of high fluorescence quantum efficiency under design composite solid state.
Summary of the invention
Object of the present invention proposes the novel fluorescent material of a class---pyrene benzimidazole derivative, there is good hole and the function of injecting of electronics simultaneously, can be directly as multi-functional luminescent material, also can be used as and inject transmission class material or host-guest material, can be for the kind of organic compound of preparing organic luminescent device thereby expanded.
A class electroluminescent organic material provided by the invention, this material is the derivative of pyrene imidazoles, it is characterized in that, this luminescent material has following general structure:
Wherein, R be H,
Figure BDA0000453074690000021
Pyrene benzimidazole derivative is the blue-fluorescence luminescent material with bipolar carrier transmission performance, and it contains triphenylamine and the carbazole unit with hole transport performance and the imidazoles unit with electronic transmission performance.Compou nd synthesis method of the present invention is simple, is suitable for widespread use.Material of the present invention has bipolar carrier transport property, can use as luminescent layer and carrier blocking layers separately, also can be dye adulterated as luminescent layer and carrier blocking layers with other.The compound the present invention relates to solution and solid-state under show stronger photoluminescent property, can form uniform film, there is good optics and thermal stability.
Described compound can be used as has one pole or bipolar carrier transmission material, thereby is applied in electroluminescent device as electroluminescent material.
Electroluminescent device of the present invention, the hole injection layer that comprises glass, be attached to Conducting Glass layer on glass, close with Conducting Glass laminating, with the hole transmission layer of hole injection layer laminating, with the luminescent layer of hole transmission layer laminating, with the hole blocking layer of luminescent layer laminating, with the electron transfer layer of hole blocking layer laminating, with the cathode layer of electron transfer layer laminating, the material of luminescent layer is compound of the present invention.Luminescent layer can also be formed as material of main part and guest materials doping by compound of the present invention, and guest materials is Ir (ppy) 3(three (2 ?phenylpyridine) close iridium), the mass concentration of its doping is 9wt%.
Accompanying drawing explanation
Fig. 1: the embodiment of the present invention 1,2,3,4 is prepared the nuclear magnetic spectrogram of material; Embodiment 1,2,3,4 is corresponding diagram 1(1 respectively), Fig. 1 (2), Fig. 1 (3), Fig. 1 (4).
Fig. 2: multilayer organic electroluminescence device structural representation of the present invention;
A class electroluminescent organic material of the present invention, can be applicable to luminescent layer or carrier blocking layers in multilayer organic electroluminescence device.
This figure is the electroluminescent device of a multilayered structure, and it 1 represents transparent glass and adhere to superincumbent conductive layer (positive pole) ITO(tin indium oxide); 6 represent metal (Al, Mg:Ag alloy, Ca, Na or K) layer (negative pole); 2,3,5 representatives are clipped in two carrier injection layer (hole injection layer 2, hole transmission layer 3 and electronic injection/transport layer 5) and the luminescent layer 4 between the two poles of the earth.
Wherein material of the present invention can be directly be applied as luminescent layer 4 as luminescent layer 4 or using main body or the guest materials of doping, and other are two-layer selects respectively hole injection/transport material (as PEDOT, NPB etc.) and electronic injection/transport material (as TPBi etc.); Material of the present invention has the character of hole injection/transport material or electronic injection/transport material simultaneously, can replace transmission class materials'use, possesses luminescent properties simultaneously.
Hole and electronics inject from positive and negative polarities respectively, transmission in hole transmission layer and electron transfer layer (being also luminescent layer) respectively, in two-layer near interface region electronics and hole-recombination, and produces exciton, exciton is got back to ground state by radiative transition, just has light to send.This radiative color can, by changing the compound change as luminescent layer application, be applied material of the present invention and can prepare blue luminescent device.Between one deck electronics injecting layer and/or electron transfer layer, electroluminescence layer and anode, can pack one deck hole injecting layer into and/or hole migrating layer is in order to improve device performance can add between electroluminescence layer and negative electrode to pack into.
The compounds of this invention has compared with hyperfluorescenceZeng Yongminggaoyingguang in solution and solid film, can form good amorphous thin film, has again goodish heat, light equistability simultaneously.In electroluminescent device applications, show higher carrier mobility ability and very high electroluminescent efficiency.
The spectrogram of the electroluminescent device of Fig. 3: embodiment 1,2,3,4 preparations; Embodiment 1,2,3,4 is corresponding diagram 3(1 respectively), Fig. 3 (2), Fig. 3 (3), Fig. 3 (4);
In example 1, can find out that by molecular structure transmitting is mainly embodied by this blue light emitting group of pyrene, thereby but because intermolecular interaction can form the red shift that some excimers cause spectrum, arrived the category of day blue light (470nm); For example 2,3, the main peak position of 4 emmission spectrum is the blue region about 450nm all, but because the oxidizing potential (0.66V) of triphenylamine is lower than the oxidizing potential (0.95V) of carbazole, thereby make example 3,4 energy gap can be slightly larger than example 2, causes so the emmission spectrum of example 3,4 can be more blue.
The efficiency luminance graph of the electroluminescent device of Fig. 4: embodiment 1,2,3,4 preparations; Embodiment 1,2,3,4 is corresponding diagram 4(1 respectively), Fig. 4 (2), Fig. 4 (3), Fig. 4 (4).
In figure left side one classify as electricity Ya ?Liang Du ?current density curve, right side one classify as electricity Liu Mi Du ? electricity stream Xiao Shuai ?power efficiency curve.The cut-in voltage of four kinds of materials is all lower, and this shows that carrier transmission performance is better; Luminous efficiency does not have too large discrepancy, no matter is current efficiency or power efficiency, can find out the brightness maximum (day blue light) of example 1 in brightness due to the difference of emmission spectrum; From current efficiency attenuation degree, example 1,3,4 increases along with current density all keep one more stable luminous, and example 2 rates of decay are than very fast, this is mainly that the rigidity of triphenylamine own and thermostability do not have carbazole to cause well.
Embodiment
Luminous organic material of the present invention, adopt containing the compound of corresponding aldehyde groups and pyrene quinone, ammonium acetate in acetic acid below heating condition legal system standby.
Compounds process for production thereof:
Embodiment 1:1,2 ?phenylbenzene replace pyrene imidazoles (PyPI)
Figure BDA0000453074690000042
Pyrene quinone (0.4g), phenyl aldehyde (0.45ml), aniline (0.5ml) and ammonium acetate (0.5g) are heated to 120 ℃ in 10ml Glacial acetic acid and reflux after two hours, stop heating, filter after being cooled to room temperature, obtain white solid, adopt SiO 2post separates, take methylene dichloride: sherwood oil volume ratio is purified and obtained white object product 0.55g, productive rate 82.5% as 1:2 crosses post.
1H?NMR(500MHz,DMSO,ppm):8.95(d,1H),8.32(d,1H),8.24(t,2H),8.19(d,2H),7.84–7.75(m,5H),7.73(d,1H),7.67(d,2H),7.43‐7.38(m,3H),7.32(d,1H)。Mass-spectrometric data (C 27h 18n 2) theoretical value: 394.5; Measured value: 394.8.Ultimate analysis (C 29h 18n 2) theoretical value: C, 88.30; H, 4.60; N, 7.10. measured value: C, 88.50; H, 4.32; N, 7.18.Show to have obtained target product.
Embodiment 2:4 ?(1 ?Ben Ji ?4,5 ?pyrene imidazoles) ?triphenylamine (PyTPAI)
Figure BDA0000453074690000051
By pyrene quinone (0.5g), 4 ?triphenylamine aldehyde (0.6g), aniline (0.5ml) and ammonium acetate (1g) in 10ml Glacial acetic acid, be heated to reflux after 2 hours in 120 ℃, stop heating, filter after being cooled to room temperature, obtain yellow-green colour solid, adopt SiO 2post separates, take methylene dichloride: sherwood oil volume ratio is purified and obtained pistac target product, productive rate 75.5% as 1:1 crosses post.
1h NMR (500MHz, DMSO, ppm): 8.93 (d, 1H), 8.31 (d, 1H), 8.25 ?8.16 (m, 4H), 7.84 ?7.75 (m, 5H), 7.74 (d, 7.6Hz, 1H), 7.55 (d, 1H), 7.36 (m, 4H), 7.27 (dd, 1H), 7.13 (t, 2H), 7.08 (d, 4H) 6.87 (d, 2H); Mass-spectrometric data (C 41h 27n 3) theoretical value: 561.67; Measured value: 562.02.Ultimate analysis (C 41h 27n 3) theoretical value: C, 87.67; H, 4.85; N, 7.48.Measured value: C, 87.44; H, 4.74; N, 7.30.Show to have obtained target product.
Embodiment 3:9 ?(1 ?Ben Ji ?4,5 ?pyrene imidazoles) ?9 ?Ben Ji ?carbazole (PyCzI)
Figure BDA0000453074690000052
By pyrene quinone (0.5g), 9 ?carbazole aldehyde (0.6g), aniline (1ml) and ammonium acetate (1g) in 10ml Glacial acetic acid, be heated to 120 ℃ reflux two hours after, stop heating, filter after being cooled to room temperature, obtain white solid, adopt SiO 2post separates, take methylene dichloride: sherwood oil volume ratio is purified and obtained white object product, productive rate 83% as 1:1 crosses post.
1h NMR (500MHz, DMSO, ppm): 8.99 (d, 1H); 8.34 (d, 1H), 8.26 (d, 2H); 8.21 (m, 4H), 7.97 (d, 2H); 7.88 (m, 5H), 7.78 (d, 1H); 7.69 (d, 2H), 7.48 ?7.32 (m; 6H), 7.30 (d, 1H); Mass-spectrometric data (C 41h 25n 3) theoretical value: 559.66; Measured value: 559.8.Ultimate analysis (C 41h 25n 3) theoretical value: C, 87.99; H, 4.50; N, 7.51.Measured value: C, 88.21; H, 4.398; N, 7.42.Show to have obtained target product.
Embodiment 4:1 phenyl, 2 ?two carbazole xenyl pyrenes imidazoles (Pyd ?CzI)
Figure BDA0000453074690000061
By pyrene quinone (0.5g), 9 ?two carbazole aldehyde (1.0g), aniline (1ml) and ammonium acetate (1g) in 10ml Glacial acetic acid, be heated to 120 ℃ reflux two hours after, stop heating, filter after being cooled to room temperature, obtain white solid, adopt SiO 2post separates, take methylene dichloride: sherwood oil volume ratio is purified and obtained target product, productive rate 63% as 1:1 crosses post.
1h NMR (500MHz, DMSO, ppm): 1H NMR (600MHz, DMSO) δ 9.01 (d; J=7.7Hz, 1H), 8.56 (s, 1H); 8.36 (dd, J=13.0,7.7Hz, 2H); 8.25 (ddd, J=26.2,16.3,8.1Hz; 6H), 8.02 (d, J=8.4Hz; 2H), 7.96 (d, J=5.7Hz; 2H), 7.87 – 7.76 (m, 6H); 7.66 (dd, J=19.6,8.6Hz; 2H), 7.54 (t, J=7.7Hz; 1H), 7.50 (d, J=8.2Hz; 1H), 7.45 (t, J=7.6Hz; 2H), 7.40 – 7.28 (m, 6H); Mass-spectrometric data (C 41h 25n 3) theoretical value: 724.85; Measured value: 724.3.Ultimate analysis (C 41h 25n 3) theoretical value: C, 87.82; H, 4.45; N, 7.73.Measured value: C, 87.63; H, 4.55; N, 7.82.Show to have obtained target product.
Embodiment 5: the preparation of electroluminescent device
Device architecture is as shown in Figure 2:
ITO/PEDOT/NPB (40nm)/luminescent layer (30nm)/TPBi (50nm)/LiF (0.75nm)/AI (100nm) can comprise glass and conductive glass (ITO) substrate layer 1, hole injection layer 2 (poly-ethylenedioxy thiophene PEDOT, 40nm), hole transmission layer 3 (4,4 ’ ?two (N ?Ben Ji ?N ?how base) ?biphenyl NPB), luminescent layer 4 (pyrene glyoxaline compound), electron transfer layer (1,3,5 ?three (1 ?Ben Ji ?1H ?Ben Mi Zuo ?2 ?base) benzene TPBi), cathode layer (lithium fluoride/aluminium).
Electroluminescent device is by methods known in the art preparation, and method as disclosed in reference (Adv.Mater.2003,15,277.) is made.Concrete grammar is: under high vacuum condition, and first spin coating one deck PEDOT on conductive glass (ITO) substrate through cleaning, then evaporation NPB, luminescent layer, TPBi, LiF and Al successively.Make device as shown in Figure 2 by the method.The electricity Liu of device ?Liang Du ?voltage characteristic completed by Keithley source measuring system (Keithley2400Sourcemeter, Keithley2000Currentmeter), electroluminescent spectrum is by the French JY SPEX CCD3000 of company spectrometer measurement, and all measurements all complete in atmosphere at room temperature.
The performance data of device sees the following form
Figure BDA0000453074690000071
Compound of the present invention is applied in electroluminescent device as luminescent layer, can obtain efficient electroluminescent properties.The present invention is using them as luminescent layer material, device 1 transmitting day blue light (470nm), device 3 to 4 is all launched blue light, peak value is positioned at 450nm left and right, the maximum current efficiency that obtains is respectively 1.55cd/A, 1.66cd/A, 1.91cd/A and 1.97cd/A, compared with other materials, multifunctional material of the present invention is owing to both containing group triphenylamine and the carbazole of hole transport performance, contain again the imidazoles unit of electronic transmission performance, be conducive to the balance of current carrier in device, obtain the electroluminescent properties of more efficient, be conducive to exploitation more high efficiency, the simple doping of device architecture and individual layer luminescent device.

Claims (5)

1. a class pyrene benzimidazole derivative, its structural formula is as follows:
Wherein, R be H,
Figure FDA0000453074680000011
2. pyrene benzimidazole derivative claimed in claim 1 is as the application of bipolar carrier transmission material.
3. pyrene benzimidazole derivative as claimed in claim 2, as the application of bipolar carrier transmission material, is characterized in that: be applied in electroluminescent device as electroluminescent material.
4. pyrene benzimidazole derivative as claimed in claim 3, as the application of bipolar carrier transmission material, is characterized in that: as the luminescent layer of electroluminescent device.
5. pyrene benzimidazole derivative as claimed in claim 4, as the application of bipolar carrier transmission material, is characterized in that: as the material of main part of luminescent layer.
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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104592125A (en) * 2015-01-24 2015-05-06 吉林大学 Pyroimidazole derivative, preparation method thereof and electroluminescent device
CN104592238A (en) * 2015-01-24 2015-05-06 吉林大学 Pyroimidazole derivative, preparation method thereof and electroluminescent device
CN107123749A (en) * 2017-04-01 2017-09-01 中山大学 A kind of high color rendering index (CRI) white light organic electroluminescent device and preparation method thereof

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101080478A (en) * 2005-06-30 2007-11-28 Lg化学株式会社 Pyrene derivatives and organic electronic device using pyrene derivatives

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101080478A (en) * 2005-06-30 2007-11-28 Lg化学株式会社 Pyrene derivatives and organic electronic device using pyrene derivatives

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104592125A (en) * 2015-01-24 2015-05-06 吉林大学 Pyroimidazole derivative, preparation method thereof and electroluminescent device
CN104592238A (en) * 2015-01-24 2015-05-06 吉林大学 Pyroimidazole derivative, preparation method thereof and electroluminescent device
CN104592238B (en) * 2015-01-24 2020-04-14 吉林大学 Pyrene imidazole derivative, preparation method thereof and electroluminescent device
CN107123749A (en) * 2017-04-01 2017-09-01 中山大学 A kind of high color rendering index (CRI) white light organic electroluminescent device and preparation method thereof

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Application publication date: 20140507